Tetrahydrofuran → HCID 18953846, compound

HRID 1491871Notes

Reaction equation

HRID 1491871 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([C:9]1[N:14]=[C:13]([C:15]2[N:16]=[C:17]([N:20]=[C:21]([NH2:23])[NH2:22])[S:18][CH:19]=2)[CH:12]=[CH:11][CH:10]=1)(=O)[NH2:7].O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.C(OCC)(=O)C>[C:6]([C:9]1[N:14]=[C:13]([C:15]2[N:16]=[C:17]([N:20]=[C:21]([NH2:23])[NH2:22])[S:18][CH:19]=2)[CH:12]=[CH:11][CH:10]=1)#[N:7]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 18953775HCID 18953775, compound

Product 1

HCID 18953846HCID 18953846, compoundYield 90.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phosphorus oxychloride (0.7 ml) was dropwise added to a mixture of 4-(6-carbamoylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole (1.0 g) in N,N-dimethylformamide (10 ml) at 2°-8° C. with stirring and the mixture was stirred for 5 hours at the same temperature. The reaction mixture was added to a mixture of tetrahydrofuran, ethyl acetate and water and the mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed by concentration and the residue was triturated with a mixture of ethyl acetate and ether to give 4-(6-cyanopyridin-2-yl)-2-(diaminomethyleneamino)-thiazole (0.84 g).

Workup

  1. stirringthe mixture was stirred for 5 hours at the same temperature
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed by concentration
  5. customthe residue was triturated with a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-76b04c91d5b24fdabd7272d2cd20a133
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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